92539-15-6

Basic information

• Product Name: 1-(2-chlorobenzyl)piperidin-4-amine
• Synonyms: 1-(2-chlorobenzyl)piperidin-4-amine;1-[(2-CHLOROPHENYL)METHYL]PIPERIDIN-4-AMINE;OTAVA-BB 1086596;1-(2-chlorobenzyl)piperidin-4-amine(SALTDATA: 2HCl)
• CAS NO: 92539-15-6
• Molecular Formula: C₁₂H₁₇ClN₂
• Molecular Weight: 224.73
• Mol File: 92539-15-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 311.6°C at 760 mmHg
• Flash Point: 142.2°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 0.000559mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: 1-(2-chlorobenzyl)piperidin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-chlorobenzyl)piperidin-4-amine(92539-15-6)
• EPA Substance Registry System: 1-(2-chlorobenzyl)piperidin-4-amine(92539-15-6)

Safety Data

• Hazardous Substances Data: 92539-15-6(Hazardous Substances Data)

Usage

Description

1-(2-chlorobenzyl)piperidin-4-amine is a chemical compound belonging to the class of amines, specifically a piperidine derivative with a chlorobenzyl group attached to the N4 amine. 1-(2-chlorobenzyl)piperidin-4-amine is known for its wide range of applications in various industries, including pharmaceuticals and agrochemicals. Its chlorobenzyl group enhances reactivity and allows for the introduction of additional functional groups, making it a versatile building block in organic synthesis. Furthermore, its potential biological activity positions it as a promising lead compound in drug discovery and development efforts.

Uses

Used in Pharmaceutical Industry:
1-(2-chlorobenzyl)piperidin-4-amine is used as an intermediate in the synthesis of various compounds with biological activity, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
1-(2-chlorobenzyl)piperidin-4-amine is used as a building block in the creation of agrochemicals, potentially leading to the development of new pesticides or other agricultural products.
Used in Organic Synthesis:
1-(2-chlorobenzyl)piperidin-4-amine is used as a versatile building block for the synthesis of a variety of organic compounds, thanks to the reactivity of its chlorobenzyl group and the ability to introduce additional functional groups through chemical reactions.
Used in Drug Discovery and Development:
1-(2-chlorobenzyl)piperidin-4-amine serves as a lead compound in drug discovery and development efforts, due to its potential biological activity and the possibility of further functionalization through chemical reactions.

InChI:InChI=1/C12H17ClN2/c13-12-4-2-1-3-10(12)9-15-7-5-11(14)6-8-15/h1-4,11H,5-9,14H2

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 39546-32-2 4-carboxamidopiperidine 
• 1286273-10-6 C₁₇H₂₅ClN₂O₂ 
• 73874-95-0 (piperidin-4-yl)carbamic acid tert-butyl ester 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 380423-94-9 4-carboxamide-1-(2-chlorobenzyl)piperidine 
• 342893-87-2 1-(o-chlorobenzyl)-4-piperidone oxime 

Downstream Products

• 76167-68-5 [1-(2-Chloro-benzyl)-piperidin-4-yl]-pyrimidin-2-yl-amine 

Relevant articles and documents

Claulansine F-donepezil hybrids as anti-alzheimer’s disease agents with cholinergic, free-radical scavenging, and neuroprotective activities

The multifactorial nature of Alzheimer’s disease (AD) calls for the development of multitarget agents addressing key pathogenic processes. A total of 26 Claulansine F-donepezil hybrids were designed and synthesized as multitarget drugs. Among these compounds, six compounds exhibited excellent acetylcholinesterase (AChE) inhibitory activity (half maximal inhibitory concentration (IC50) 1.63-4.62 μM). Moreover, (E)-3-(8-(tert-Butyl)-3,3-dimethyl-3,11-dihydropyrano[3,2-a]carbazol- 5-yl)-N-((1-(2-chlorobenzyl)piperidin-4-yl)methyl)acrylamide (6bd) exhibited better neuroprotective effects against OGD/R (oxygen-glucose deprivation/reoxygenation) than lead compound Claulansine F. Furthermore, 6bd could cross the blood-brain barrier in vitro. More importantly, compared to edaravone, 6bd had stronger free-radical scavenging activity. Molecular docking studies revealed that 6bd could interact with the catalytic active site of AChE. All of these outstanding in vitro results indicate 6bd as a leading structure worthy of further investigation.

Piperidinyl Ureas Chemically Control Defective in Cullin Neddylation 1 (DCN1)-Mediated Cullin Neddylation

We previously discovered and validated a class of piperidinyl ureas that regulate defective in cullin neddylation 1 (DCN1)-dependent neddylation of cullins. Here, we report preliminary structure-activity relationship studies aimed at advancing our high-throughput screen hit into a tractable tool compound for dissecting the effects of acute DCN1-UBE2M inhibition on the NEDD8/cullin pathway. Structure-enabled optimization led to a 100-fold increase in biochemical potency and modestly increased solubility and permeability as compared to our initial hit. The optimized compounds inhibit the DCN1-UBE2M protein-protein interaction in our TR-FRET binding assay and inhibit cullin neddylation in our pulse-chase NEDD8 transfer assay. The optimized compounds bind to DCN1 and selectively reduce steady-state levels of neddylated CUL1 and CUL3 in a squamous cell carcinoma cell line. Ultimately, we anticipate that these studies will identify early lead compounds for clinical development for the treatment of lung squamous cell carcinomas and other cancers.

6,9-DISUBSTITUTED 2- TRANS-(4- AMINOCYCLOHEXYL) AMINO]PURINES

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